Diisopropylethylamine → HCID 86709420, compound

HRID 882251Notes

Reaction equation

[NH2:1][C@H:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([Br:12])[CH:10]=2)[N:5]([C:13](=[O:15])[CH3:14])[C@@H:4]([CH3:16])[CH2:3]1.Cl[C:18]1[N:19]=[CH:20][C:21]([C:24]#[N:25])=[N:22][CH:23]=1.CCN(C(C)C)C(C)C>CN1C(=O)CCC1>[C:13]([N:5]1[C:6]2[C:11](=[CH:10][C:9]([Br:12])=[CH:8][CH:7]=2)[C@H:2]([NH:1][C:18]2[N:19]=[CH:20][C:21]([C:24]#[N:25])=[N:22][CH:23]=2)[CH2:3][C@@H:4]1[CH3:16])(=[O:15])[CH3:14]

Participants

Conditions

Temperature: 200 °C

Procedure

1-((2S,4R)-4-amino-6-bromo-2-methyl-3,4-dihydroquinolin-1(2H)-yl)ethanone (for a preparation, see Intermediate 1) (50 mg, 0.177 mmol), 5-chloropyrazine-2-carbonitrile (37.0 mg, 0.265 mmol) and DIPEA (0.123 mL, 0.706 mmol) were combined in NMP (1.5 mL) and heated in a sealed flask under microwave irradiation to 200° C. for 1 h. The mixture was partitioned between water (150 mL) and EtOAc (4×100 mL). The organic layers were combined, washed with brine (2×100 mL), dried by passing through a hydrophobic frit, and concentrated in vacuo. The resulting residue was purified by chromatography (25 g column, EtOAc/cyclohexane gradient) to give 5-(((2S,4R)-1-acetyl-6-bromo-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl)amino)pyrazine-2-carbonitrile (61 mg, 0.158 mmol, 89% yield) as a brown gum.

Workup

customThe mixture was partitioned between water (150 mL) and EtOAc (4×100 mL)
washwashed with brine (2×100 mL)
customdried
concentrationconcentrated in vacuo
customThe resulting residue was purified by chromatography (25 g column, EtOAc/cyclohexane gradient)

Sources & evidence

ORD record: ord-8a56fdf5524f439ca2a14adc7c2f25f7
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08993554B2

Reaction notes

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